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Water → 1-[2-Acetyl-4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]tetrahydro-1(2H)-pyridazinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

HRID 75175
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HRID 75175 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]1[O:13][N:12]=[C:11]([C:14]2[N:15]=[C:16]([CH:19]3[CH2:24][CH2:23][N:22]([C:25](=[O:37])[CH2:26][N:27]4[C:31]([CH3:32])=[CH:30][C:29]([C:33]([F:36])([F:35])[F:34])=[N:28]4)[NH:21][CH2:20]3)[S:17][CH:18]=2)[CH2:10]1.O.[C:39](OC(=O)C)(=[O:41])[CH3:40]>>[C:39]([N:21]1[CH2:20][CH:19]([C:16]2[S:17][CH:18]=[C:14]([C:11]3[CH2:10][CH:9]([C:3]4[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=4[F:8])[O:13][N:12]=3)[N:15]=2)[CH2:24][CH2:23][N:22]1[C:25](=[O:37])[CH2:26][N:27]1[C:31]([CH3:32])=[CH:30][C:29]([C:33]([F:35])([F:36])[F:34])=[N:28]1)(=[O:41])[CH3:40]
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참가 물질

4

반응물 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 866744671-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]tetrahydro-1(2H)-pyridazinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

생성물 1

HCID 866744661-[2-Acetyl-4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]tetrahydro-1(2H)-pyridazinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

반응 조건

온도
100 °C

실험 절차

A mixture of 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3 isoxazolyl]-2-thiazolyl]tetrahydrol(2H)-pyridazinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (i.e. the product of Example 1) (0.24 g, 0.44 mmol) in acetic anhydride (2 mL) was heated at 100° C. overnight. The reaction mixture was cooled, water (30 mL) was added and the mixture was stirred for 30 min and then extracted with ethyl acetate. The ethyl acetate extract was washed with saturated aqueous sodium bicarbonate solution and saturated sodium chloride solution, dried over magnesium sulfatate, filtered, and concentrated under reduced pressure. The resulting material was purified by silica gel chromatography (0-100% gradient of ethyl acetate in hexane as eluant) to provide the title compound (150 mg), a compound of the present invention, as a dark foam.

후처리

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with saturated aqueous sodium bicarbonate solution and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfatate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting material was purified by silica gel chromatography (0-100% gradient of ethyl acetate in hexane as eluant)

출처 및 근거

ORD 기록
ord-ad74ab3709834021a4e224070fa4c269
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08835427B2

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